CN101560152A - Method for synthesizing propionate - Google Patents
Method for synthesizing propionate Download PDFInfo
- Publication number
- CN101560152A CN101560152A CNA2009100273135A CN200910027313A CN101560152A CN 101560152 A CN101560152 A CN 101560152A CN A2009100273135 A CNA2009100273135 A CN A2009100273135A CN 200910027313 A CN200910027313 A CN 200910027313A CN 101560152 A CN101560152 A CN 101560152A
- Authority
- CN
- China
- Prior art keywords
- propionic acid
- reaction
- propionate
- catalyst
- synthesizing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 108
- 238000006243 chemical reaction Methods 0.000 claims abstract description 55
- 235000019260 propionic acid Nutrition 0.000 claims abstract description 54
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims abstract description 37
- 150000001336 alkenes Chemical class 0.000 claims abstract description 21
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 12
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 12
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 21
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 claims description 11
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical group CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 claims description 10
- 238000007259 addition reaction Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- -1 isopropyl ester Chemical class 0.000 claims description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 7
- 239000002351 wastewater Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 208000012839 conversion disease Diseases 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000002245 particle Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 230000009466 transformation Effects 0.000 description 12
- 238000001914 filtration Methods 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229920000557 Nafion® Polymers 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Cycle index | 1 | 2 | 3 | 4 | 5 |
The propionic acid transformation efficiency | 88.4% | 89.1% | 87.7% | 88.5% | 89.6% |
The isopropyl propionate selectivity | 97.8% | 98.1% | 98.5% | 97.6% | 97.9% |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100273135A CN101560152B (en) | 2009-05-27 | 2009-05-27 | Method for synthesizing propionate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100273135A CN101560152B (en) | 2009-05-27 | 2009-05-27 | Method for synthesizing propionate |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101560152A true CN101560152A (en) | 2009-10-21 |
CN101560152B CN101560152B (en) | 2012-05-23 |
Family
ID=41219157
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009100273135A Expired - Fee Related CN101560152B (en) | 2009-05-27 | 2009-05-27 | Method for synthesizing propionate |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101560152B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104761450A (en) * | 2012-12-20 | 2015-07-08 | 常州市松盛香料有限公司 | Preparation method of ethyl propionate |
CN106316840A (en) * | 2016-08-23 | 2017-01-11 | 深圳市普利凯新材料股份有限公司 | Method for preparing and purifying tertbutyl propionate |
CN114940648A (en) * | 2022-06-30 | 2022-08-26 | 常州夏青科技有限公司 | Method for preparing mono-tert-butyl malonate by catalysis of strong acid resin |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69117871T2 (en) * | 1990-10-31 | 1996-11-07 | Daicel Chem | Process for the preparation of a lower alkyl acetate |
CN100432039C (en) * | 2007-07-11 | 2008-11-12 | 胡先念 | Method for protective preparation of acidic ion exchange resin catalyst for lower fatty acid ester |
-
2009
- 2009-05-27 CN CN2009100273135A patent/CN101560152B/en not_active Expired - Fee Related
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104761450A (en) * | 2012-12-20 | 2015-07-08 | 常州市松盛香料有限公司 | Preparation method of ethyl propionate |
CN104761450B (en) * | 2012-12-20 | 2016-08-24 | 常州市松盛香料有限公司 | The preparation method of ethyl propionate |
CN106316840A (en) * | 2016-08-23 | 2017-01-11 | 深圳市普利凯新材料股份有限公司 | Method for preparing and purifying tertbutyl propionate |
CN114940648A (en) * | 2022-06-30 | 2022-08-26 | 常州夏青科技有限公司 | Method for preparing mono-tert-butyl malonate by catalysis of strong acid resin |
CN114940648B (en) * | 2022-06-30 | 2023-11-21 | 常州夏青科技有限公司 | Method for preparing malonic acid mono-tert-butyl ester by catalysis of strong acid resin |
Also Published As
Publication number | Publication date |
---|---|
CN101560152B (en) | 2012-05-23 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: NANJING TOP CHEMICAL CO., LTD. Free format text: FORMER OWNER: NANJING UNIVERSITY OF TECHNOLOGY Effective date: 20131115 |
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C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 210009 NANJING, JIANGSU PROVINCE TO: 210047 NANJING, JIANGSU PROVINCE |
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TR01 | Transfer of patent right |
Effective date of registration: 20131115 Address after: 210047 Nanjing chemical industry park, Liuhe District, Jiangsu, West Road, No. 179 Patentee after: NANJING TOP CHEMICAL Co.,Ltd. Address before: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Patentee before: Nanjing Tech University |
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CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 210047 Nanjing Chemical Industrial Park West Road, Jiangsu, No. 179 Patentee after: NANJING TOP CHEMICAL TECHNOLOGY Co.,Ltd. Address before: 210047 Nanjing chemical industry park, Liuhe District, Jiangsu, West Road, No. 179 Patentee before: NANJING TOP CHEMICAL Co.,Ltd. |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180503 Address after: 238200 No. 6, Chao three road, Ma'anshan County, Anhui province. Patentee after: Anhui Hua Pu ester Mstar Technology Ltd. Address before: 210047 No. 179 West Road, Nanjing Chemical Industrial Park, Jiangsu Patentee before: NANJING TOP CHEMICAL TECHNOLOGY Co.,Ltd. |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190425 Address after: 211500 West Road, Changlu Street Park, Jiangbei New District, Nanjing City, Jiangsu Province, 179 Patentee after: NANJING TOP CHEMICAL TECHNOLOGY Co.,Ltd. Address before: 238200 No. 6, Chao three road, Ma'anshan County, Anhui province. Patentee before: Anhui Hua Pu ester Mstar Technology Ltd. |
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TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20220216 Address after: 211599 13 / F, main building, science and innovation center, 59 Wangqiao Road, Xiongzhou street, Liuhe District, Nanjing City, Jiangsu Province Patentee after: Nanjing Zihuan Engineering Technology Research Institute Co.,Ltd. Address before: 211500 West Road, Changlu Street Park, Jiangbei New District, Nanjing City, Jiangsu Province, 179 Patentee before: NANJING TOP CHEMICAL TECHNOLOGY Co.,Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120523 |